HRP20110434T1 - Spojevi pirazolo[3,4-b]piridina i njihova upotreba kao inhibitora pde4 - Google Patents

Spojevi pirazolo[3,4-b]piridina i njihova upotreba kao inhibitora pde4 Download PDF

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HRP20110434T1
HRP20110434T1 HR20110434T HRP20110434T HRP20110434T1 HR P20110434 T1 HRP20110434 T1 HR P20110434T1 HR 20110434 T HR20110434 T HR 20110434T HR P20110434 T HRP20110434 T HR P20110434T HR P20110434 T1 HRP20110434 T1 HR P20110434T1
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methyl
amino
pyrazolo
pyridin
diethyl
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George Allen David
Mary Aston Nicola
Phillip Barnett Rodger
Manesh Chudasama Reshma
Jane Day Caroline
David Edlin Christopher
Jane Kindon Leanda
Trivedi Naimisha
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Glaxo Group Limited
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Priority claimed from GB0714815A external-priority patent/GB0714815D0/en
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Abstract

Spoj formule (I), ili njegova sol: naznačen time što Ar ima podformulu (x): gdje: Q1 je NH ili NMe, u kom slučaju Q2 je -C(O)-, -S(O)2-, -C(O)NH- ili -C(O)NMe-;ili Q1 je veza ili -O-, u kom slučaju Q2 je veza; ili Q1 je -C(O)-, u kom slučaju Q2 je NH ili NMe; ili Q1 je -S(O)2-, u kom slučaju Q2 je NH, NMe ili veza; i L je (CH2)n, gdje n je 4, 5, 6, 7, 8, 9, 10, 11, 12 ili 13; ili L je -(CH2)m1-O-(CH2)m2-, gdje je upravo -(CH2)m2- vezan na skupinu NR5R6, te gdje m1 je 1, 2, 3,4, 5, 6, 7, 8 ili 9, a m2 je 2, 3,4, 5, 6, 7, 8 ili 9; uz uvjet da m1+m2 je 3, 4, 5, 6, 7, 8, 9, 10, 11 ili 12, te uz uvjet da kada m1 je 1, Q2 je -C(O)-; i R5 je atom vodika (H), metil, etil, n-propil, izopropil, -CH2CH2OH -CH2CH(Me)OH, -CH2CH2CH2OH, -CH2CH2OMe ili -CH2CH2CH2OMe; iR6 je C1-4alkil, ili R6 je C1-4alkil, supstituiran s jednim supstituentom OH ili OC1-3alkil koji nije supstituiran na alkilnom atomu ugljika vezanom na atom dušika u skupini NR5R6;ili R5 i R6 uzeti zajedno su -(CH2)2-X-(CH2)2-, -(CH2)2-X-(CH2)3-, -(CH2)p1-, -CHR7a-(CH2)p2- ili -(CH2)p3-CHR7b-(CH2)p4-; gdje: X je O ili NR8, gdje R8 je atom vodika (H) ili C1-3alkil; R7a je -CH2OH, -CH2OC1-3alkil, -CH2CH2OH, -CH2CH2OC1-3alkil, ili C1-3alkil; R7b je OH, OC1-3alkil, -CH2OH, -CH2OC1-3alkil, -CH2CH2OH, -CH2CH2OC1-3alkil ili C1-3alkil; p1 je 4, 5 ili 6, p2 je 3, 4 ili 5, p3 je 1 ili 2, a p4 je 2, 3 ili 4, uz uvjet da p3+p4 je 3, 4 ili 5; te gdje: R1 je C1-3alkil, -CH2-C1-2fluoralkil ili -CH2CH2OH; R2 je atom vodika (H), metil, etil, n-propil, izopropil, n-butil, C1-2fluoralkil, ciklopropil, ciklobutil ili (ciklopropil)metil-;R4 je atom vodika (H), metil ili etil; iR3 je izborno supstituirani C4-7cikloalkil, ili izborno supstituirani mononezasićeni-C5-7cikloalkenil, ili izborno supstituirana heterociklička skupina s podformulom (aa), (bb) ili (cc), ili biciklička skupina s podformulom (ee); gdje n1 i n2 neovisno su 1 ili 2; te gdje Y je O, S, SO2, ili NR10; gdje R10 je atom vodika (H), metil, C(O)NH2, C(O)-metil ili C(O)-C1fluoralkil; te gdje, kada R3 je izborno supstituirani C4-7cikloalkil, R3 je C4-7cikloalkil, izborno supstituiran na jednom ili više ugljika u prstenu s jednim ili dva supstituenta, koji su neovisno: okso (=O); OH; metoksi; C1fluoralkoksi; NH2; C1-2alkil; C1fluoralkil; -CH2OH -CH(Me)OH; -CH2CH2OH; -CH2NH2; -C(O)OH; -C(O)NHR24, gdje R24 je H ili metil; -C(O)R25, gdje R25 je metil; fluor; hidroksiimino (=N-OH); ili (C1-2alkoksi)imino (=N-OR26, gdje R26 je C1-2alkil); te gdje bilo koji OH, metoksi, fluoralkoksi ili NH2 supstituent nije vezan na R3 ugljik u prstenu vezan na skupinu -NH- u formuli (I); te gdje, kada R3 je izborno supstituirana heterociklička skupina s podformulom (aa), (bb) ili (cc), R3 je heterociklička skupina s podformulom (aa), (bb) ili (cc), izborno supstituirana na jednom ili više ugljika u prstenu s jednim ili dva okso (=O) supstituenta; te gdje, kada R3 je izborno supstituirani mononezasićeni-C5-7cikloalkenil, cikloalkenil je izborno supstituiran na ugljiku u prstenu s

Claims (20)

1. Spoj formule (I), ili njegova sol: [image] naznačen time što Ar ima podformulu (x): [image] gdje: Q1 je NH ili NMe, u kom slučaju Q2 je -C(O)-, -S(O)2-, -C(O)NH- ili -C(O)NMe-; ili Q1 je veza ili -O-, u kom slučaju Q2 je veza; ili Q1 je -C(O)-, u kom slučaju Q2 je NH ili NMe; ili Q1 je -S(O)2-, u kom slučaju Q2 je NH, NMe ili veza; i L je (CH2)n, gdje n je 4, 5, 6, 7, 8, 9, 10, 11, 12 ili 13; ili L je -(CH2)m1-O-(CH2)m2-, gdje je upravo -(CH2)m2- vezan na skupinu NR5R6, te gdje m1 je 1, 2, 3,4, 5, 6, 7, 8 ili 9, a m2 je 2, 3,4, 5, 6, 7, 8 ili 9; uz uvjet da m1+m2 je 3, 4, 5, 6, 7, 8, 9, 10, 11 ili 12, te uz uvjet da kada m1 je 1, Q2 je -C(O)-; i R5 je atom vodika (H), metil, etil, n-propil, izopropil, -CH2CH2OH -CH2CH(Me)OH, -CH2CH2CH2OH, -CH2CH2OMe ili -CH2CH2CH2OMe; i R6 je C1-4alkil, ili R6 je C1-4alkil, supstituiran s jednim supstituentom OH ili OC1-3alkil koji nije supstituiran na alkilnom atomu ugljika vezanom na atom dušika u skupini NR5R6; ili R5 i R6 uzeti zajedno su -(CH2)2-X-(CH2)2-, -(CH2)2-X-(CH2)3-, -(CH2)p1-, -CHR7a-(CH2)p2- ili -(CH2)p3-CHR7b-(CH2)p4-; gdje: X je O ili NR8, gdje R8 je atom vodika (H) ili C1-3alkil; R7a je -CH2OH, -CH2OC1-3alkil, -CH2CH2OH, -CH2CH2OC1-3alkil, ili C1-3alkil; R7b je OH, OC1-3alkil, -CH2OH, -CH2OC1-3alkil, -CH2CH2OH, -CH2CH2OC1-3alkil ili C1-3alkil; p1 je 4, 5 ili 6, p2 je 3, 4 ili 5, p3 je 1 ili 2, a p4 je 2, 3 ili 4, uz uvjet da p3+p4 je 3, 4 ili 5; te gdje: R1 je C1-3alkil, -CH2-C1-2fluoralkil ili -CH2CH2OH; R2 je atom vodika (H), metil, etil, n-propil, izopropil, n-butil, C1-2fluoralkil, ciklopropil, ciklobutil ili (ciklopropil)metil-; R4 je atom vodika (H), metil ili etil; i R3 je izborno supstituirani C4-7cikloalkil, ili izborno supstituirani mononezasićeni-C5-7cikloalkenil, ili izborno supstituirana heterociklička skupina s podformulom (aa), (bb) ili (cc), ili biciklička skupina s podformulom (ee); [image] gdje n1 i n2 neovisno su 1 ili 2; te gdje Y je O, S, SO2, ili NR10; gdje R10 je atom vodika (H), metil, C(O)NH2, C(O)-metil ili C(O)-C1fluoralkil; te gdje, kada R3 je izborno supstituirani C4-7cikloalkil, R3 je C4-7cikloalkil, izborno supstituiran na jednom ili više ugljika u prstenu s jednim ili dva supstituenta, koji su neovisno: okso (=O); OH; metoksi; C1fluoralkoksi; NH2; C1-2alkil; C1fluoralkil; -CH2OH -CH(Me)OH; -CH2CH2OH; -CH2NH2; -C(O)OH; -C(O)NHR24, gdje R24 je H ili metil; -C(O)R25, gdje R25 je metil; fluor; hidroksiimino (=N-OH); ili (C1-2alkoksi)imino (=N-OR26, gdje R26 je C1-2alkil); te gdje bilo koji OH, metoksi, fluoralkoksi ili NH2 supstituent nije vezan na R3 ugljik u prstenu vezan na skupinu -NH- u formuli (I); te gdje, kada R3 je izborno supstituirana heterociklička skupina s podformulom (aa), (bb) ili (cc), R3 je heterociklička skupina s podformulom (aa), (bb) ili (cc), izborno supstituirana na jednom ili više ugljika u prstenu s jednim ili dva okso (=O) supstituenta; te gdje, kada R3 je izborno supstituirani mononezasićeni-C5-7cikloalkenil, cikloalkenil je izborno supstituiran na ugljiku u prstenu s jednim supstituentom, koji je fluor ili metil, a R3 ugljik u prstenu vezan na skupinu -NH- u formuli (I) ne sudjeluje u cikloalkenilnoj dvostrukoj vezi; te gdje: kada R3 je heterociklička skupina s podformulom (aa), a Y je NR10, R10 nije C(O)-metil ili C(O)-C1fluoralkil; i kada R3 je heterociklička skupina s podformulom (bb), a Y je NR10, R10 nije metil; i kada R3 je heterociklička skupina s podformulom (cc), Y je O, S, SO2 ili NR10, gdje R10 je H ili metil; te gdje: kada R3 je izborno supstituirani C4-7cikloalkil, bilo koji supstituent -C(O)NHR24 ili -C(O)R25 na ugljiku u prstenu je: na položaju 3 za R3 u ciklobutilnom prstenu; ili na položaju 3 ili 4 za R3 u ciklopentilnom prstenu; ili na položaju 4 za R3 u cikloheksilnom prstenu; ili na položaju 3, 4, 5 ili 6 za R3 u cikloheptilnom prstenu (gdje, u vezi s tim, položaj 1 za R3 u cikloalkilnom prstenu se uzima kao mjesto vezanja na -NH- u formuli (I), tj. atom u prstenu vezan na -NH- u formuli (I)); te gdje: kada R3 je izborno supstituirani C4-7cikloalkil, bilo koji supstituent OH, metoksi, fluoralkoksi, -CH2OH, -CH(Me)OH, -CH2CH2OH, -CH2NH2 ili -C(O)OH na ugljiku u prstenu je: na položaju 3 za R3 u ciklobutilnom prstenu; ili na položaju 3 ili 4 za R3 u ciklopentilnom prstenu; ili na položaju 3, 4 ili 5 za R3 u cikloheksilnom prstenu; ili na položaju 3, 4, 5 ili 6 za R3 u cikloheptilnom prstenu.
2. Spoj ili sol u skladu s patentnim zahtjevom 1, naznačen time što R1 je etil.
3. Spoj ili sol u skladu s patentnim zahtjevom 1 ili patentnim zahtjevom 2, naznačen time što R2 je etil.
4. Spoj ili sol u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što R3 je heterociklička skupina s podformulom (bb), a n1 je 1.
5. Spoj ili sol u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što NHR3 ima podformulu (c), (h), (k2), (k3), (n), (o), (o2), (p9) ili (p13). [image]
6. Spoj, ili njegova sol, u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što R4 je atom vodika (H).
7. Spoj, ili njegova sol, u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što Ar ima podformulu (x1): [image]
8. Spoj, ili njegova sol, u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što Q1 je NH ili NMe, u kom slučaju Q2 je -C(O)-; ili Q1 je veza, u kom slučaju Q2 je veza; ili Q1 je -C(O)-, u kom slučaju Q2 je NH ili NMe.
9. Spoj, ili njegova sol, u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što L je (CH2)n.
10. Spoj, ili njegova sol, u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što n je 6, 7, 8 ili 9.
11. Spoj, ili njegova sol, u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što: R5 je atom vodika (H), metil, etil, n-propil, izopropil ili -CH2CH2OH; i R6 je -CH2CH2OH, -CH2CH(Me)OH, -CH2CH2CH2OH, -CH2CH2CH2CH2OH, -CH2CH2OMe ili -CH2CH2CH2OMe; ili R5 i R6 se uzima zajedno i jesu -(CH2)2-X-(CH2)2-, -(CH2)p1- ili -CHR7a-(CH2)p2-.
12. Spoj, ili njegova sol, u skladu s patentnim zahtjevom 1, naznačen time što je: N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({8-[(2-hidroksietil)(metil)amino]oktanoil}amino)benzamid, 4-[(1,6-dietil-5-{[({4-[(8-{(2R)-2-[(metiloksi)metil]-1-pirolidinil}oktanoil)amino]fenil}karbonil)amino]metil}-1H-pirazolo[3,4-b]piridin-4-il)amino]-1-piperidinkarboksamid, 4-[(1,6-dietil-5-{[({4-[{8-{(2S)-2-[(metiloksi)metil]-1-pirolidinil}oktanoil)amino]fenil}karbonil)amino]metil}-1H-pirazolo[3,4-b]piridin-4-il)amino]-1-piperidinkarboksamid, 4-({1,6-dietil-5-[({[4-({8-[(2-hidroksietil)(metil)amino]oktanoil}amino)fenil]karbonil}amino)metil]-1H-pirazolo[3,4-b]piridin-4-il}amino)-1-piperidinkarboksamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-[(8-{(2R)-2-[(metiloksi)metil]-1-pirolidinil}oktanoil)amino]benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-[(8-{(2S)-2-[(metiloksi)metil]-1-pirolidinil}oktanoil)amino]benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-{[8-(4-morfolinil)oktanoil]amino}benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-{[8-(1-pirolidinil)oktanoil]amino}benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-[4-({4-[(2-hidroksietil)(metil)amino]butil}oksi)butil]benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-(4-{[4-(4-morfolinil)butil]oksi}butil)benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-(4-{[4-(1-pirolidinil)butil]oksi}butil)benzamid, 4-[(1,6-dietil-5-{[({4-[4-({4-[(2-hidroksietil)(metil)amino]butil}oksi)butil]fenil}karbonil)amino]metil}-1H-pirazolo[3,4-b]piridin-4-il)amino]-1-piperidinkarboksamid, 4-({1,6-dietil-5-[({[4-(4-{[4-(4-morfolinil)butil]oksi}butil)fenil]karbonil}amino)metil]-1H-pirazolo[3,4-b]piridin-4-il}amino)-1-piperidinkarboksamid, 4-({1,6-dietil-5-[({[4-(4-{[4-(1-pirolidinil)butil]oksi}butil)fenil]karbonil}amino)metil]-1H-pirazolo[3,4-b]piridin-4-il}amino)-1-piperidinkarboksamid, N-{[1-etil-6-metil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({8-[(2-hidroksietil)(metil)amino]oktanoil}amino)benzamid, N-{[1-etil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({8-[(2-hidroksietil)(metil)amino]oktanoil}amino)benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-[8-(4-morfolinil)oktil]benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-{8-[(2-hidroksietil)(metil)amino]oktil}benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-3-({8-[(2-hidroksietil)(metil)amino]oktanoil}amino)benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-2-({8-[(2-hidroksietil)(metil)amino]oktanoil}amino)benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({6-[(2-hidroksietil)(metil)amino]heksanoil}amino)benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({7-[(2-hidroksietil)(metil)amino]heptanoil}amino)benzamid, N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({10-[(2-hidroksietil)(metil)amino]dekanoil}amino)benzamid, ili N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({11-[(2-hidroksietil)(metil)amino]undekanoil}amino)benzamid; ili njihove soli, primjerice njihove farmaceutski prihvatljive soli.
13. Spoj, ili njegova sol, u skladu s patentnim zahtjevom 12, naznačen time što je: N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({8-[(2-hidroksietil)(metil)amino]oktanoil}amino)benzamid, formule [image] ili njegova farmaceutski prihvatljiva sol.
14. Spoj, ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevom 13, naznačen time što je: N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({8-[(2-hidroksietil)(metil)amino]oktanoil}amino)benzamid.
15. Spoj, ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevom 13, naznačen time što je: N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({8-[(2-hidroksietil)(metil)amino]oktanoil}amino)benzamid-hidroklorid.
16. Spoj, ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevom 13, naznačen time što je: N-{[1,6-dietil-4-(tetrahidro-2H-piran-4-ilamino)-1H-pirazolo[3,4-b]piridin-5-il]metil}-4-({8-[(2-hidroksietil)(metil)amino]oktanoil}amino)benzamid-monohidroklorid ili -dihidroklorid.
17. Spoj, ili njegova farmaceutski prihvatljiva sol, u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što je namijenjen upotrebi kao aktivna terapijska tvar za sisavca.
18. Upotreba spoja formule (I), ili njegove farmaceutski prihvatljive soli, u skladu s bilo kojim od patentnih zahtjeva 1 do 16, naznačena time što je navedeni spoj namijenjen proizvodnji medikamenta za liječenje i/ili profilaksu upalne i/ili alergijske bolesti kod sisavca.
19. Spoj formule (I), ili njegova farmaceutski prihvatljiva sol, u skladu s bilo kojim od patentnih zahtjeva 1 do 16, naznačen time što je namijenjen upotrebi u liječenju i/ili profilaksi upalne i/ili alergijske bolesti kod sisavca.
20. Spoj formule (I), ili njegova farmaceutski prihvatljiva sol, u skladu s bilo kojim od patentnih zahtjeva 1 do 16, naznačen time što je namijenjen upotrebi u liječenju i/ili profilaksi: kronične opstruktivne plućne bolesti (COPD), astme, rinitisa (primjerice alergijskog i/ili nealergijskog rinitisa), reumatoidnog artritisa, atopičnog dermatitisa, psorijaze, koprivnjače, alergijskog konjunktivitisa, proljetnog konjunktivitisa, eozinofilnog granuloma, septičnog šoka, upalne bolesti crijeva (primjerice ulceroznog kolitis i/ili Crohnove bolesti), reperfuzijske ozljede miokarda i mozga, kroničnog glomerulonefritisa, endotoksičnog šoka ili sindroma respiratornog distresa kod odraslih, kod sisavca, poput čovjeka.
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